#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:45:22 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180052 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/46/7034636.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7034636
loop_
_publ_author_name
'Mohamed, Heba A.'
'Lake, Benjamin R. M.'
'Laing, Thomas'
'Phillips, Roger M.'
'Willans, Charlotte E.'
_publ_section_title
;
 Synthesis and anticancer activity of silver(i)-N-heterocyclic carbene
 complexes derived from the natural xanthine products caffeine,
 theophylline and theobromine.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7563
_journal_page_last               7569
_journal_paper_doi               10.1039/c4dt03679d
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C16 H17 Ag N4 O4'
_chemical_formula_sum            'C16 H17 Ag N4 O4'
_chemical_formula_weight         437.21
_chemical_name_systematic        3d
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-12-01 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;
_cell_angle_alpha                82.181(6)
_cell_angle_beta                 86.063(6)
_cell_angle_gamma                67.816(6)
_cell_formula_units_Z            2
_cell_length_a                   8.7170(6)
_cell_length_b                   9.9462(6)
_cell_length_c                   10.2712(9)
_cell_measurement_reflns_used    3053
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      30.2020
_cell_measurement_theta_min      3.5250
_cell_volume                     816.79(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28e (release 10-06-2013 CrysAlis171 .NET)
(compiled Jun 10 2013,11:58:50)
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_computing_structure_refinement
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M.    Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector_area_resol_mean 5.3095
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0853
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6438
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         3.17
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.264
_exptl_absorpt_correction_T_max  0.9280
_exptl_absorpt_correction_T_min  0.7861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0191P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0836
_reflns_number_gt                3452
_reflns_number_total             4023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4dt03679d2.cif
_cod_data_source_block           Complex3d
_cod_depositor_comments
'Adding full bibliography for 7034631--7034636.cif.'
_cod_original_cell_volume        816.79(10)
_cod_database_code               7034636
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ag1 Ag -0.06603(3) 0.86483(3) 0.05082(3) 0.01453(9) Uani 1 1 d .
O1 O -0.0926(3) 1.3862(2) 0.5572(3) 0.0175(6) Uani 1 1 d .
O2 O 0.3413(3) 0.9822(2) 0.4483(3) 0.0186(6) Uani 1 1 d .
O3 O -0.1351(3) 0.7504(2) -0.0783(3) 0.0185(6) Uani 1 1 d .
O4 O 0.1366(3) 0.6418(3) -0.1007(3) 0.0232(6) Uani 1 1 d .
N1 N -0.1555(3) 1.0867(3) 0.2577(3) 0.0111(6) Uani 1 1 d .
N2 N -0.1494(3) 1.2475(3) 0.4223(3) 0.0116(6) Uani 1 1 d .
N3 N 0.1242(3) 1.1884(3) 0.4981(3) 0.0130(6) Uani 1 1 d .
N4 N 0.1061(3) 0.9519(3) 0.2550(3) 0.0111(6) Uani 1 1 d .
C1 C -0.3297(4) 1.1474(4) 0.2150(4) 0.0193(8) Uani 1 1 d .
H1A H -0.3404 1.0980 0.1418 0.029 Uiso 1 1 calc R
H1B H -0.3627 1.2524 0.1865 0.029 Uiso 1 1 calc R
H1C H -0.4015 1.1320 0.2885 0.029 Uiso 1 1 calc R
C2 C -0.0380(4) 0.9755(3) 0.1984(4) 0.0117(7) Uani 1 1 d .
C3 C -0.0818(4) 1.1369(3) 0.3445(4) 0.0109(7) Uani 1 1 d .
C4 C -0.3255(4) 1.3431(4) 0.4224(4) 0.0207(9) Uani 1 1 d .
H4A H -0.3517 1.4060 0.3383 0.031 Uiso 1 1 calc R
H4B H -0.3486 1.4040 0.4942 0.031 Uiso 1 1 calc R
H4C H -0.3936 1.2832 0.4346 0.031 Uiso 1 1 calc R
C5 C -0.0422(4) 1.2819(3) 0.4953(4) 0.0126(7) Uani 1 1 d .
C6 C 0.2321(4) 1.2294(4) 0.5762(4) 0.0175(8) Uani 1 1 d .
H6A H 0.2230 1.3296 0.5449 0.026 Uiso 1 1 calc R
H6B H 0.3473 1.1624 0.5665 0.026 Uiso 1 1 calc R
H6C H 0.1978 1.2232 0.6690 0.026 Uiso 1 1 calc R
C7 C 0.1974(4) 1.0651(3) 0.4309(4) 0.0123(7) Uani 1 1 d .
C8 C 0.0839(4) 1.0503(3) 0.3455(4) 0.0101(7) Uani 1 1 d .
C9 C 0.2646(4) 0.8552(3) 0.2070(4) 0.0123(7) Uani 1 1 d .
C10 C 0.3845(4) 0.9131(4) 0.1632(4) 0.0148(8) Uani 1 1 d .
H10 H 0.3666 1.0123 0.1699 0.018 Uiso 1 1 calc R
C11 C 0.5301(4) 0.8217(4) 0.1100(4) 0.0177(8) Uani 1 1 d .
H11 H 0.6142 0.8585 0.0812 0.021 Uiso 1 1 calc R
C12 C 0.5566(4) 0.6776(4) 0.0975(4) 0.0192(8) Uani 1 1 d .
H12 H 0.6576 0.6165 0.0603 0.023 Uiso 1 1 calc R
C13 C 0.4339(4) 0.6234(3) 0.1400(4) 0.0179(8) Uani 1 1 d .
H13 H 0.4506 0.5251 0.1308 0.021 Uiso 1 1 calc R
C14 C 0.2875(4) 0.7117(3) 0.1957(4) 0.0173(8) Uani 1 1 d .
H14 H 0.2041 0.6744 0.2257 0.021 Uiso 1 1 calc R
C15 C -0.0065(4) 0.6536(3) -0.1223(4) 0.0152(8) Uani 1 1 d .
C16 C -0.0369(5) 0.5487(4) -0.2014(4) 0.0283(10) Uani 1 1 d .
H16A H 0.0645 0.4975 -0.2502 0.042 Uiso 1 1 calc R
H16B H -0.1263 0.6033 -0.2633 0.042 Uiso 1 1 calc R
H16C H -0.0687 0.4773 -0.1419 0.042 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C2 Ag1 O3 168.94(11) .
C2 Ag1 Ag1 65.18(9) 2_575
O3 Ag1 Ag1 123.36(7) 2_575
C15 O3 Ag1 110.0(2) .
C2 N1 C3 110.2(3) .
C2 N1 C1 120.8(3) .
C3 N1 C1 128.6(3) .
C3 N2 C5 118.2(3) .
C3 N2 C4 123.8(3) .
C5 N2 C4 117.6(3) .
C5 N3 C7 126.5(3) .
C5 N3 C6 115.4(3) .
C7 N3 C6 118.0(3) .
C2 N4 C8 110.9(3) .
C2 N4 C9 122.4(3) .
C8 N4 C9 125.6(3) .
N1 C1 H1A 109.5 .
N1 C1 H1B 109.5 .
H1A C1 H1B 109.5 .
N1 C1 H1C 109.5 .
H1A C1 H1C 109.5 .
H1B C1 H1C 109.5 .
N4 C2 N1 105.6(3) .
N4 C2 Ag1 125.3(2) .
N1 C2 Ag1 129.1(2) .
N2 C3 C8 122.5(3) .
N2 C3 N1 130.4(3) .
C8 C3 N1 107.1(3) .
N2 C4 H4A 109.5 .
N2 C4 H4B 109.5 .
H4A C4 H4B 109.5 .
N2 C4 H4C 109.5 .
H4A C4 H4C 109.5 .
H4B C4 H4C 109.5 .
O1 C5 N3 121.1(3) .
O1 C5 N2 121.4(3) .
N3 C5 N2 117.5(3) .
N3 C6 H6A 109.5 .
N3 C6 H6B 109.5 .
H6A C6 H6B 109.5 .
N3 C6 H6C 109.5 .
H6A C6 H6C 109.5 .
H6B C6 H6C 109.5 .
O2 C7 N3 121.8(3) .
O2 C7 C8 126.3(3) .
N3 C7 C8 111.9(3) .
C3 C8 N4 106.1(3) .
C3 C8 C7 122.6(3) .
N4 C8 C7 131.3(3) .
C14 C9 C10 121.8(3) .
C14 C9 N4 119.2(3) .
C10 C9 N4 118.8(3) .
C11 C10 C9 117.9(3) .
C11 C10 H10 121.1 .
C9 C10 H10 121.1 .
C10 C11 C12 121.7(3) .
C10 C11 H11 119.2 .
C12 C11 H11 119.2 .
C11 C12 C13 119.3(3) .
C11 C12 H12 120.4 .
C13 C12 H12 120.4 .
C14 C13 C12 120.5(3) .
C14 C13 H13 119.8 .
C12 C13 H13 119.8 .
C9 C14 C13 118.9(3) .
C9 C14 H14 120.5 .
C13 C14 H14 120.5 .
O4 C15 O3 123.2(3) .
O4 C15 C16 120.8(3) .
O3 C15 C16 116.0(3) .
C15 C16 H16A 109.5 .
C15 C16 H16B 109.5 .
H16A C16 H16B 109.5 .
C15 C16 H16C 109.5 .
H16A C16 H16C 109.5 .
H16B C16 H16C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 C2 2.068(4) .
Ag1 O3 2.111(3) .
Ag1 Ag1 3.3249(5) 2_575
O1 C5 1.213(4) .
O2 C7 1.223(4) .
O3 C15 1.273(4) .
O4 C15 1.240(4) .
N1 C2 1.373(4) .
N1 C3 1.378(4) .
N1 C1 1.480(4) .
N2 C3 1.371(4) .
N2 C5 1.400(5) .
N2 C4 1.469(4) .
N3 C5 1.396(4) .
N3 C7 1.403(4) .
N3 C6 1.475(4) .
N4 C2 1.346(4) .
N4 C8 1.393(4) .
N4 C9 1.453(4) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C3 C8 1.375(4) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C7 C8 1.425(5) .
C9 C14 1.385(5) .
C9 C10 1.395(4) .
C10 C11 1.380(5) .
C10 H10 0.9500 .
C11 C12 1.385(5) .
C11 H11 0.9500 .
C12 C13 1.390(5) .
C12 H12 0.9500 .
C13 C14 1.385(5) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C16 1.513(5) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C2 Ag1 O3 C15 -140.9(5) .
Ag1 Ag1 O3 C15 80.6(2) 2_575
C8 N4 C2 N1 -2.6(4) .
C9 N4 C2 N1 -171.6(3) .
C8 N4 C2 Ag1 176.5(2) .
C9 N4 C2 Ag1 7.5(4) .
C3 N1 C2 N4 3.7(4) .
C1 N1 C2 N4 177.0(3) .
C3 N1 C2 Ag1 -175.4(2) .
C1 N1 C2 Ag1 -2.1(4) .
O3 Ag1 C2 N4 136.2(5) .
Ag1 Ag1 C2 N4 -81.4(3) 2_575
O3 Ag1 C2 N1 -44.9(7) .
Ag1 Ag1 C2 N1 97.5(3) 2_575
C5 N2 C3 C8 6.5(5) .
C4 N2 C3 C8 179.2(3) .
C5 N2 C3 N1 -175.6(3) .
C4 N2 C3 N1 -2.9(5) .
C2 N1 C3 N2 178.4(3) .
C1 N1 C3 N2 5.8(6) .
C2 N1 C3 C8 -3.4(4) .
C1 N1 C3 C8 -176.0(3) .
C7 N3 C5 O1 -179.9(3) .
C6 N3 C5 O1 -2.4(5) .
C7 N3 C5 N2 2.5(5) .
C6 N3 C5 N2 180.0(3) .
C3 N2 C5 O1 173.7(3) .
C4 N2 C5 O1 0.6(5) .
C3 N2 C5 N3 -8.6(4) .
C4 N2 C5 N3 178.2(3) .
C5 N3 C7 O2 -173.5(3) .
C6 N3 C7 O2 9.0(5) .
C5 N3 C7 C8 5.6(5) .
C6 N3 C7 C8 -171.8(3) .
N2 C3 C8 N4 -179.9(3) .
N1 C3 C8 N4 1.7(4) .
N2 C3 C8 C7 2.4(5) .
N1 C3 C8 C7 -176.0(3) .
C2 N4 C8 C3 0.6(4) .
C9 N4 C8 C3 169.2(3) .
C2 N4 C8 C7 178.0(3) .
C9 N4 C8 C7 -13.4(5) .
O2 C7 C8 C3 171.1(3) .
N3 C7 C8 C3 -8.0(4) .
O2 C7 C8 N4 -6.0(6) .
N3 C7 C8 N4 174.9(3) .
C2 N4 C9 C14 -55.7(5) .
C8 N4 C9 C14 136.9(4) .
C2 N4 C9 C10 119.1(4) .
C8 N4 C9 C10 -48.3(5) .
C14 C9 C10 C11 -1.3(6) .
N4 C9 C10 C11 -175.8(3) .
C9 C10 C11 C12 1.2(6) .
C10 C11 C12 C13 -0.2(6) .
C11 C12 C13 C14 -0.8(6) .
C10 C9 C14 C13 0.3(6) .
N4 C9 C14 C13 174.9(3) .
C12 C13 C14 C9 0.7(6) .
Ag1 O3 C15 O4 -6.7(4) .
Ag1 O3 C15 C16 171.8(2) .
